3-(3-Nitrophenyl)-1-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one

The molecule of the title compound is almost planar but with a dihedral angle between the two phenyl rings of 19.22 (5)°. In the crystal, molecules are linked by C—H⋯O interactions, forming sheets in the (21 ) plane.


Structure description
Chalcones are among the leading bioactive flavonoids, with a therapeutic potential implicated to an array of bioactivities that have been investigated by a series of preclinical and clinical studies. They contain anunsaturated carbonyl system, which is present in open-chain form, and two aromatic rings are joined through three-carbon atoms (Kozlowski et al., 2007;Raghav & Garg, 2014). Studies depicting the biological activities of chalcones and their derivatives describe their immense significance as antidiabetic, anticancer, anti-inflammatory, antimicrobial, antioxidant, antiparasitic, psychoactive and neuroprotective agents, and their antioxidant and enzyme inhibitory activities (Lin et al., 2002;Bhat et al., 2005;Trivedi et al., 2007;Lahtchev et al., 2008;Aneja et al., 2018).
The present work describes the synthesis and crystal structure of the title compound 3-(3-nitrophenyl)-1-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one ( Fig. 1), which crystallizes in the triclinic space group P1 with one molecule in the asymmetric unit. It consists both a 3-nitrophenyl group and a (prop-2-yn-1-yloxy)benzene group linked to a central chalcone moiety. Even though the C-N bond length is 1.4706 (17) Å and thus single, the nitro group is almost coplanar with its phenyl ring [dihedral angle of 18.94 (6) ] as a result of the steric clash between O1 and H4 and between O2 and H2, respectively. The chalcone group is planar (average deviation from plane of 0.004 Å ) and makes dihedral angles of 7.69 (8) and 10.96 (6) with the 3-nitrophenyl ring and the phenyl ring of the (prop-2-yn-1-yloxy)benzene group, respectively. Lastly, the twist between the two phenyl rings which are linked by the chalcone is 19.22 (5) .
The molecules are linked by C-HÁ Á ÁO interactions (Table 1), which form sheets in the (211) plane as shown in Fig. 2. There are nointeractions between the phenyl rings.

Figure 2
Packing diagram for the title compound showing the C-HÁ Á ÁO interactions linking the molecules into sheets in the (211) plane.

Figure 1
Diagram of molecules showing the atom-labelling scheme. Atomic displacement parameters are at the 30% probability level.

Refinement
Crystal data, data collection and structure refinement details for the title compound are summarized in Table 2.

data-1
IUCrData (   where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.28 e Å −3 Δρ min = −0.21 e Å −3 Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. data reports data-2 IUCrData (2022). 7, x220957 Refinement. The acetylenic H atom was freely refined. All remaining hydrogen atoms were placed geometrically and refined as riding atoms with their U iso values 1.2 times that of their attached atoms.